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$43+ Cheap flights from Chesapeake, VA to Massachusetts

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 1/15. Fares are subject to change and may not be available on all flights or dates of travel.
RIC — BOS
ene. 22 — ene. 291
jue. 1/22
jue. 1/29
1 adult, Economy
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Cheap flight deals from Chesapeake to Massachusetts

Cheapest flights from Chesapeake to Massachusetts
Explore the most affordable flight options available from Chesapeake to Massachusetts. Find the lowest fares from popular airlines and budget airlines, with prices last updated on diciembre 23, 2025.

This Booking.com deal was found by Cheapflights users on 12/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mar. 12/3010:27 amORF - BDL
Nonstop1h 27mBreeze Airways
dom. 1/117:15 amBDL - ORF
Nonstop1h 38mBreeze Airways
Deal found 12/21$133
This Booking.com deal was found by Cheapflights users on 12/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mar. 12/3010:27 amORF - BDL
Nonstop1h 27mBreeze Airways
jue. 1/17:15 amBDL - ORF
Nonstop1h 37mBreeze Airways
Deal found 12/21$161
This Booking.com deal was found by Cheapflights users on 12/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mar. 12/2310:27 amORF - BDL
Nonstop1h 27mBreeze Airways
dom. 1/47:15 amBDL - ORF
Nonstop1h 37mBreeze Airways
Deal found 12/21$208
This Kiwi.com deal was found by Cheapflights users on 12/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mié. 12/315:46 pmORF - BDL
2 stops29h 57mBreeze Airways
dom. 1/117:15 amBDL - ORF
Nonstop1h 38mBreeze Airways
Deal found 12/22$239
This Kiwi.com deal was found by Cheapflights users on 12/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mar. 12/3010:27 amORF - BDL
Nonstop1h 27mMultiple Airlines
dom. 1/113:00 pmBDL - ORF
2 stops27h 38mMultiple Airlines
Deal found 12/21$245
This Breeze Airways deal was found by Cheapflights users on 12/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Breeze Airways is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
lun. 12/299:25 pmORF - BDL
Nonstop1h 27mBreeze Airways
mar. 12/308:10 amBDL - ORF
Nonstop1h 37mBreeze Airways
Deal found 12/22$248
This Breeze Airways deal was found by Cheapflights users on 12/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Breeze Airways is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mar. 12/2310:27 amORF - BDL
Nonstop1h 27mBreeze Airways
jue. 12/257:15 amBDL - ORF
Nonstop1h 37mBreeze Airways
Deal found 12/23$268
This Kiwi.com deal was found by Cheapflights users on 12/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mié. 12/313:01 pmORF - BDL
3 stops32h 01mMultiple Airlines
dom. 1/117:15 amBDL - ORF
Nonstop1h 38mMultiple Airlines
Deal found 12/22$282
This United Airlines deal was found by Cheapflights users on 12/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mié. 12/317:55 pmORF - BOS
1 stop3h 59mUnited Airlines
dom. 1/47:32 pmBOS - ORF
1 stop4h 02mUnited Airlines
Deal found 12/21$332
This United Airlines deal was found by Cheapflights users on 12/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
lun. 12/2911:41 amORF - BOS
1 stop3h 54mUnited Airlines
mié. 12/315:20 amBOS - ORF
1 stop4h 35mUnited Airlines
Deal found 12/21$337
This American Airlines deal was found by Cheapflights users on 12/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mar. 12/3010:07 amORF - BOS
1 stop6h 30mAmerican Airlines
jue. 1/89:30 amBOS - ORF
1 stop5h 26mAmerican Airlines
Deal found 12/22$372
This United Airlines deal was found by Cheapflights users on 12/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
lun. 12/296:00 amORF - BOS
1 stop6h 43mUnited Airlines
dom. 1/47:44 pmBOS - ORF
1 stop3h 57mUnited Airlines
Deal found 12/22$383

Find flight deals from Chesapeake to Massachusetts

Keep the following information in mind while searching for Chesapeake to Massachusetts flight deals. Data was last updated diciembre 23, 2025.

Most accurate provider

CheapOair
3 stars

Most trusted provider

CheapOair
3 stars

Round-trip from

$81
(Booking.com)

One-way from

$43
(Booking.com)

Popular in

November

Cheapest in

July

Average price

$316
Provider with most accurate pricing for Norfolk-Boston Logan Intl flight deals.
Search Deals
Provider most trusted by Cheapflights users for Norfolk-Boston Logan Intl flights.
Search Deals
From Chesapeake to Massachusetts
Search Deals
One-way flight from Chesapeake to Massachusetts
Search Deals
Highest demand for flights based on searches. 16% potential increase in price ($50 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 5% potential price decrease ($14 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in December 2025
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from Chesapeake to Massachusetts that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated diciembre 23, 2025.
Use the filters below to find and compare flights from Chesapeake to Massachusetts that are best for you.

Fly from

Chesapeake

Fly to

Massachusetts

Route

Depart

Return

Price

NorfolkHartford

ORF - BDL

ORFBDL

Norfolk

jue. 1/15

9:04 pm-10:31 pm

Nonstop1h 27m

Hartford Bradley Intl

lun. 1/19

7:00 am-8:38 am

Nonstop1h 38m

$81

NorfolkHartford

ORF - BDL

ORFBDL

Norfolk

jue. 1/15

9:04 pm-10:31 pm

Nonstop1h 27m

Hartford Bradley Intl

vie. 1/16

7:00 am-8:38 am

Nonstop1h 38m

$86

NorfolkBoston

ORF - BOS

ORFBOS

Norfolk

jue. 2/5

4:01 pm-11:19 pm

1 stop7h 18m

Boston Logan Intl

sáb. 2/7

7:00 am-8:15 pm

1 stop13h 15m

$129

NorfolkBoston

ORF - BOS

ORFBOS

Norfolk

mar. 2/17

7:31 pm-10:26 am

1 stop14h 55m

Boston Logan Intl

lun. 2/23

5:27 am-6:26 pm

1 stop12h 59m

$137

NorfolkHartford

ORF - BDL

ORFBDL

Norfolk

jue. 1/15

6:45 am-11:56 pm

2 stops17h 11m

Hartford Bradley Intl

lun. 1/19

7:00 am-8:38 am

Nonstop1h 38m

$139

NorfolkBoston

ORF - BOS

ORFBOS

Norfolk

vie. 1/23

7:33 pm-4:28 pm

1 stop20h 55m

Boston Logan Intl

mar. 1/27

3:43 pm-6:25 pm

1 stop26h 42m

$142

NorfolkHartford

ORF - BDL

ORFBDL

Norfolk

sáb. 6/13

10:30 pm-11:59 pm

Nonstop1h 29m

Hartford Bradley Intl

dom. 6/21

8:00 am-9:31 am

Nonstop1h 31m

$148

NorfolkBoston

ORF - BOS

ORFBOS

Norfolk

jue. 2/5

4:01 pm-11:19 pm

1 stop7h 18m

Boston Logan Intl

dom. 2/8

5:34 am-6:38 pm

1 stop13h 04m

$152

NorfolkBoston

ORF - BOS

ORFBOS

Norfolk

jue. 2/5

7:33 pm-2:38 pm

2 stops19h 05m

Boston Logan Intl

sáb. 2/7

7:00 am-9:50 pm

1 stop14h 50m

$153

NorfolkHartford

ORF - BDL

ORFBDL

Norfolk

mié. 1/21

8:40 am-4:03 pm

2 stops31h 23m

Hartford Bradley Intl

dom. 1/25

7:15 am-8:53 am

Nonstop1h 38m

$159

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/21

Showing 1-10 of 60 results
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Best time to book a flight from Chesapeake to Massachusetts

Have a flexible travel schedule? Discover the best time to fly to Massachusetts from Chesapeake with our price prediction graph.
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Cheapflights Insights

Everything you need to know about your flight from Chesapeake to Massachusetts

What is the cheapest month to book a flight from Chesapeake to Massachusetts?

Currently, July is the cheapest month in which you can book a flight from Chesapeake to Massachusetts (average of $50). Flying from Chesapeake to Massachusetts in November is currently the most expensive (average of $115). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

What is the cheapest time of day to fly from C6E to MA?

Find hourly flight availability from Chesapeake to Massachusetts. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated diciembre 23, 2025.

It’s optimal to fly from Chesapeake to Massachusetts in the afternoon. By choosing this option you can save up to 40% on the cost of your flight, compared to a flight at noon.

What is the cheapest day to fly from Chesapeake to Massachusetts?

Use this chart to determine the cheapest time to fly round-trip from Chesapeake to Massachusetts. Price data was last updated on December 16, 2024.

Travelers seeking maximum savings on their Chesapeake to Massachusetts flight should consider departing on Friday evenings when fares are most often at their lowest. Saturday at noon flights should be avoided if possible as fares are typically the most expensive at this time.

Weekly flight availability from Chesapeake to Massachusetts

Explore weekly flight availability from Chesapeake to Massachusetts. Discover flights operating on different days of the week, giving you the flexibility to choose a travel day that best fits your plans. Compare info to find the most convenient option for your journey. Data last updated diciembre 23, 2025.

The most flights from C6E to USMA are scheduled on a Sunday (19 on average). You will have fewer flight options on Wednesday, which is when the least amount of flights are scheduled (7 on average).

Reviews of airlines servicing Massachusetts

Get insights into the airlines that provide service to Massachusetts. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Massachusetts. Reviews last updated diciembre 23, 2025.
Peruse reviews from past customers who have flown with Delta, United Airlines, and American Airlines from Chesapeake to Massachusetts to help guide your decision. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Delta
7.9
Good
8,014 reviews

Food

7.3

Entertainment

7.9

Boarding

8.1

Overall

7.9

Crew

8.5

Comfort

7.9

Reviews

1 / 20
6.0
Good

Jim,Nov 2025

AVL - ATL

The exit row seats without a seat in front are great for leg room but don’t have a fold out entertainment console so you’re forced to use the screen several feet in front of you (there is, at least, a remote). Best to bring a tablet loaded with entertainment or a book.
Delta
7.9
Good
8,014 reviews
Delta
7.9
Good
8,014 reviews

Food

7.3

Entertainment

7.9

Boarding

8.1

Overall

7.9

Crew

8.5

Comfort

7.9

Reviews

1 / 20
6.0
Good

Jim,Nov 2025

AVL - ATL

The exit row seats without a seat in front are great for leg room but don’t have a fold out entertainment console so you’re forced to use the screen several feet in front of you (there is, at least, a remote). Best to bring a tablet loaded with entertainment or a book.
United Airlines
7.4
Good
9,105 reviews
Delta
7.9
Good
8,014 reviews

Food

7.3

Entertainment

7.9

Boarding

8.1

Overall

7.9

Crew

8.5

Comfort

7.9

Reviews

1 / 20
6.0
Good

Jim,Nov 2025

AVL - ATL

The exit row seats without a seat in front are great for leg room but don’t have a fold out entertainment console so you’re forced to use the screen several feet in front of you (there is, at least, a remote). Best to bring a tablet loaded with entertainment or a book.
American Airlines
7.2
Good
11,054 reviews
Delta
7.9
Good
8,014 reviews

Food

7.3

Entertainment

7.9

Boarding

8.1

Overall

7.9

Crew

8.5

Comfort

7.9

Reviews

1 / 20
6.0
Good

Jim,Nov 2025

AVL - ATL

The exit row seats without a seat in front are great for leg room but don’t have a fold out entertainment console so you’re forced to use the screen several feet in front of you (there is, at least, a remote). Best to bring a tablet loaded with entertainment or a book.
JetBlue
7.2
Good
2,897 reviews
Delta
7.9
Good
8,014 reviews

Food

7.3

Entertainment

7.9

Boarding

8.1

Overall

7.9

Crew

8.5

Comfort

7.9

Reviews

1 / 20
6.0
Good

Jim,Nov 2025

AVL - ATL

The exit row seats without a seat in front are great for leg room but don’t have a fold out entertainment console so you’re forced to use the screen several feet in front of you (there is, at least, a remote). Best to bring a tablet loaded with entertainment or a book.
Allegiant Air
7.2
Good
701 reviews
Delta
7.9
Good
8,014 reviews

Food

7.3

Entertainment

7.9

Boarding

8.1

Overall

7.9

Crew

8.5

Comfort

7.9

Reviews

1 / 20
6.0
Good

Jim,Nov 2025

AVL - ATL

The exit row seats without a seat in front are great for leg room but don’t have a fold out entertainment console so you’re forced to use the screen several feet in front of you (there is, at least, a remote). Best to bring a tablet loaded with entertainment or a book.

Related info for your journey

Find useful and relevant information for your journey from Chesapeake to Massachusetts. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • How popular is this Chesapeake to Massachusetts flight route?

    Within the past month, 27 users have taken a look at flights from Chesapeake to Massachusetts.

  • How long is the flight from Chesapeake to Massachusetts?

    Airlines like Breeze Airways, Spirit Airlines, and Delta fly from Chesapeake to Massachusetts in about 1h 27m. The time it takes to get you to your destination can typically vary by up to 13h 28m. The distance between Chesapeake and Massachusetts is about 395 mi. Both multi-stop and nonstop flights can be found to your destination and back.

  • What are the cheapest airlines to fly from Chesapeake to Massachusetts one-way?

    For one-way options, check prices for Spirit Airlines. According to our data, you can fly for as low as $44. Users have also found prices from $48 and $73 on Allegiant Air and JetBlue, respectively.

  • What are the most popular routes from Chesapeake to Massachusetts?

    When deciding which route to take from Chesapeake to Massachusetts consider Norfolk - Boston Logan Intl, Norfolk - Hartford Bradley Intl or Norfolk - Albany Intl as they are the most popular.

  • What are the most reliable airlines from Chesapeake to Massachusetts?

    Looking for the most reliable airlines to get you to your destination on time? Our data shows these are most likely to get you from Chesapeake to Massachusetts on time: United Airlines (100%), WestJet (100%), Etihad Airways (92%).

  • What are the cheapest flights from Chesapeake to Massachusetts?

    The cheapest flight price from Chesapeake to Massachusetts is $78. On average you can expect to pay $774. The most popular route, (Norfolk - Boston Logan Intl), can usually be booked for $129.

  • Can I find deals for flights from Chesapeake to Massachusetts that include hotel bookings?

    Yes. In addition to deals on Chesapeake to Massachusetts flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Chesapeake to Massachusetts?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Chesapeake to Massachusetts.

  • Can I find deals for business class flights from Chesapeake to Massachusetts?

    Yes. Cheapflights offers flight deals from Chesapeake to Massachusetts by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

  • What is the cheapest month to book a flight from Chesapeake to Massachusetts?

    Currently, July is the cheapest month in which you can book a flight from Chesapeake to Massachusetts (average of $50). Flying from Chesapeake to Massachusetts in November is currently the most expensive (average of $115). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

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Alternative routes for Chesapeake to Massachusetts

See prices for flight routes from nearby airports that may be better suited for you.
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Top 8 airlines flying from Chesapeake to Massachusetts

Discover the top 8 airlines that operate flights from Chesapeake to Massachusetts. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated diciembre 23, 2025.
AirlineCheapestAverageFlexibilityOn-time
Allegiant AirCheapest$48Average$89FlexibilityNo cancel feeOn-time88%
Breeze AirwaysCheapest$82Average$149FlexibilityNo cancel feeOn-timeN/A
Spirit AirlinesCheapest$85Average$175FlexibilityNo cancel feeOn-time65%
JetBlueCheapest$93Average$248FlexibilityNo cancel feeOn-time62%
DeltaCheapest$100Average$265FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$154Average$324FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$156Average$317FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$166Average$333FlexibilityNo cancel feeOn-time63%

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